Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1-Undecyne | HCID 75249 | — |
| Reactant | 3-Bromobenzaldehyde | HCID 76583 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-(1-Undecynyl)benzaldehyde | HCID 18373091 | 109.1% |
Reaction Steps
To a solution of 3-bromobenzaldehyde (30.3 g) and 1-undecyne (29.5 g) in triethylamine (120 ml) was added bis(triphenylphosphine)palladium(II) chloride (1.9 g) followed by copper(I) iodide (0.25 g). The mixture was stirred in the dark at 55° C. for 6 hrs, under nitrogen. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and filtered. The filtrate was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated to yield 45.8 g of 3-(1-undecynyl)benzaldehyde, as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05977147 |
|---|
| Source dataset | uspto-grants-1999_11 |
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| ORD ID | ord-ae8f3093f27a427fb25393f17d7dff0b |
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| Source note | uspto-grants-1999_11 |
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